CN101398413B - Liquid phase analytical method for iminodiacetic acid - Google Patents
Liquid phase analytical method for iminodiacetic acid Download PDFInfo
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Abstract
The invention provides a liquid-phase analyzing method of iminodiacetic acid. The method comprises the following steps of: (1) preparing the standard solution of the iminodiacetic acid with different concentration, adding enough 2, 4-dinitrofluorobenzene for reaction, carrying out liquid chromatographic analysis to the reaction liquid after the reaction is ended and drawing a standard curve by the peak area of DNB-iminodiacetic acid corresponding to the concentration of the iminodiacetic acid; and (2) adding enough 2, 4-dinitrofluorobenzene into the iminodiacetic acid-containing solution to be detected for reaction, carrying out liquid chromatographic analysis to the reaction liquid after the reaction is ended, and obtaining the data of the concentration of the iminodiacetic acid solution to be detected by being contrasted with a standard curve obtained in the step (1) and according to the peak area of DNB-iminodiacetic acid. The invention has accurate method, good reproducibility and high sensitivity, can be used for the analysis of products produced in the process of producing the iminodiacetic acid of glyphosate intermediates by carrying out biocatalysis and hydrolysis to iminodiacetonitrile and can also be used for the analysis of the production process of other iminodiacetic acid.
Description
(1) technical field
The present invention relates to the liquid phase analysis method of iminodiacetic acid.
(2) background technology
Iminodiacetic acid (IDA) is a kind of important industrial chemicals, uses always and makes complexing agent and surfactant, is usually used in being used for organic synthesis, also is the important intermediate that glyphosate (Glyphosate) is produced.
The analytical approach that iminodiacetic acid is commonly used at present has: alkali direct titrimetric method, ion-exchange-resin process, ultraviolet spectrophotometry and chromatography.Because iminodiacetic acid is an organic dibasic acid, what adopt alkali direct titrimetric method mensuration is the content of (comprising single acid) of all acid in the sample, and accuracy is poor; Ion-exchange-resin process is owing to separation, the difficult grasp of wash-out degree, so result's reappearance is poor; Ultraviolet spectrophotometry needs iron alum and IDA elder generation generation complex to detect again, and method is more loaded down with trivial details; Itself does not have ultraviolet absorption group iminodiacetic acid, and conventional liquid phase process can only detect under 210nm, and the interference ratio that the end that receives absorbs is bigger.
(3) summary of the invention
The objective of the invention is to overcome the terminal defective of disturbing that absorbs of conventional liquid phase, provide a kind of the absorption to disturb little, highly sensitive iminodiacetic acid liquid phase analysis method.
The technical scheme that the present invention adopts is:
The liquid phase analysis method of iminodiacetic acid; Said method comprises: the iminodiacetic acid standard solution of (1) preparation variable concentrations; Add capacity 2 separately; The 4-dinitrofluorobenzene is in reacting, and reaction finishes the back reactant liquor is carried out liquid-phase chromatographic analysis, with the corresponding oxalic acid concentration of DNB-iminodiacetic acid peak area drawing standard curve; (2) get the solution to be measured that contains iminodiacetic acid; Add capacity 2; The 4-dinitrofluorobenzene reacts, and reaction finishes the back reactant liquor is carried out liquid-phase chromatographic analysis, according to the peak area of DNB-iminodiacetic acid; Contrast the typical curve that step (1) obtains, obtain the iminodiacetic acid concentration data of solution to be measured.
The present invention carries out derivatization to iminodiacetic acid, and on its amino, introducing the dinitro benzene group increases absorbing wavelength, and its reaction principle is shown below:
Further, said method is following:
(1) the iminodiacetic acid standard solution of preparation variable concentrations; Add capacity 2 separately; The 4-dinitrofluorobenzene reacts 20～40min under 40～70 ℃, lucifuge condition; Reaction finishes the back reactant liquor is carried out liquid-phase chromatographic analysis, is that ordinate, iminodiacetic acid (salt) acid concentration are horizontal ordinate with DNB-iminodiacetic acid peak area, the drawing standard curve;
(2) get the solution to be measured that contains iminodiacetic acid; Add capacity 2; The 4-dinitrofluorobenzene reacts 20～40min under 40～70 ℃, lucifuge condition, reaction finishes the back reactant liquor is carried out liquid-phase chromatographic analysis, according to the peak area of DNB-iminodiacetic acid to be measured; Contrast the typical curve that step (1) obtains, obtain the iminodiacetic acid concentration data of solution to be measured.
Preferably, said method is following:
(1) the iminodiacetic acid standard solution of preparation variable concentrations is got the standard solution of 1 parts by volume, adds the NaHCO of 0.1～1mol/L of 10 parts by volume separately
32 of the volumetric concentration 1～10% of solution, 4 parts by volume; The distilled water of 4-dinitrofluorobenzene acetonitrile solution and 10 parts by volume; Behind 40～70 ℃ of following lucifuge reaction 20～40min, the 0.1～0.5mol/L, the pH that add 75 parts by volume again are 6～8 phosphate buffer, and the mixed liquor that obtains carries out liquid-phase chromatographic analysis; With DNB-iminodiacetic acid peak area is that ordinate, iminodiacetic acid (salt) acid concentration are horizontal ordinate, the drawing standard curve;
(2) get solution to be measured 1 parts by volume that contains iminodiacetic acid, add the NaHCO of 0.1～1mol/L of 10 parts by volume
32 of the volumetric concentration 1～10% of solution, 4 parts by volume; The distilled water of 4-dinitrofluorobenzene acetonitrile solution and 10 parts by volume, behind 40～70 ℃ of following lucifuge reaction 20～40min, the 0.1～0.5mol/L, the pH that add 75 parts by volume again are 6～8 phosphate buffer; The mixed liquor that obtains carries out liquid-phase chromatographic analysis; According to the peak area of DNB-iminodiacetic acid to be measured, contrast the typical curve that step (1) obtains, obtain the iminodiacetic acid concentration data of solution to be measured.
By guaranteeing the accuracy of institute's survey data, a complete process that is plotted to solution concentration mensuration to be measured from typical curve, for the standard solution and the solution to be measured of variable concentrations, each step parameter should be identical in its mensuration process.
The solution concentration to be measured of surveying needs in institute's drawing standard curve concentration range; Recording data is only accurately; If solution concentration to be measured exceeds the concentration range of typical curve; Then might not meet its linear relationship, detect after can or concentrating solution dilution to be measured this moment, till measured concentration is in the typical curve concentration range.
The scheme that the present invention adopts is:
1, the configuration of derivatization reagent:
Get 1～10mL2, the 4-dinitrofluorobenzene is dissolved in and is made into 100mL solution in the acetonitrile.
2, derivative reaction:
Get 0.1～0.5mL sample, add the NaHCO of 0.5～2mL0.1～1mol/L
3Solution, 0.1～1mL prepare 2,4-dinitrofluorobenzene acetonitrile solution and 0.5～2mL distilled water, behind 40～70 ℃ of following lucifuges reaction 20～40min, adding 5～20mL0.1～0.5mol/L pH again is 6～8 phosphate buffer.
3, chromatographic condition:
Chromatographic column: Elite C18 chromatographic column (250nm * 4.6nm);
Moving phase: methyl alcohol: acetate-aqueous sodium acetate solution (methyl alcohol and acetate-aqueous sodium acetate solution volume ratio is 55:45, and acetate, sodium acetate amount of substance concentration are 0.05mol/L); Flow velocity: 0.5～1.5mL/min; The detection wavelength is 300～400nm;
Column temperature: 20～40 ℃;
4, instrument and equipment of the present invention
The HPLC chromatographic work station that day island proper Tianjin 10A vp of company liquid chromatography configuration SPD-10A UV-detector and analytical instrument are equipped with;
Specifications of raw materials of the present invention is following:
Methyl alcohol, acetonitrile (chromatographically pure)
2,4-dinitrofluorobenzene, acetate, sodium acetate (analyzing pure)
Beneficial effect of the present invention is mainly reflected in: the inventive method is accurate, favorable reproducibility, highly sensitive; Can be used for living things catalysis hydrolysis iminodiacetonitrile and produce the product analysis of glyphosate intermedium iminodiacetic acid, also can also be used for the analysis of other iminodiacetic acid production runes.
(4) description of drawings
Fig. 1 is the iminodiacetic acid canonical plotting;
Fig. 2 is the DNB-iminodiacetic acid that obtains after deriving and the chromatographic peak of derivatization reagent.
(5) embodiment
Below in conjunction with specific embodiment the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1: the iminodiacetic acid typical curve is drawn
Accurately the iminodiacetic acid standard solution of preparation 2,4,6,8,10mg/mL is got the NaHCO that titer 0.1mL adds 1.0mL1mol/L separately
3Solution, 0.4mL prepare 2; 4-dinitrofluorobenzene acetonitrile solution (volumetric concentration 6%) and 1.0mL distilled water; Behind 60 ℃ of following lucifuges reaction 30min, add 7.5mL 0.2mol/L pH again and be 7.0 phosphate buffer, filter with syringe filters; Get filtrating by selected chromatographic condition: Elite C18 chromatographic column; Moving phase: methyl alcohol: 0.05mol/L acetate-sodium acetate solution (methyl alcohol and acetate-sodium acetate solution volume ratio 55:45), flow velocity: 1.0mL/min, sample introduction 10 μ L carry out liquid-phase chromatographic analysis.With DNB-iminodiacetic acid peak area is independent variable, and iminodiacetic acid (salt) acid concentration (mg/mL) is a dependent variable, and it is as shown in Figure 1 to obtain typical curve shape figure, its linear R
2Value is 0.9990, and chromatogram is as shown in Figure 2.
Embodiment 2: the iminodiacetic acid sample concentration is confirmed
Accurately take by weighing 0.5008g iminodiacetic acid sample dissolution in 100mL water, get the NaHCO that this sample 0.2mL adopts 2mL 1mol/L
3Solution, 0.8mL prepare 2,4-dinitrofluorobenzene acetonitrile solution (volumetric concentration 1%) and 2mL distilled water behind 70 ℃ of following lucifuges reaction 40min, add 15mL 0.2mol/L pH and are 7.5 phosphate buffer again.Filter with syringe filters.Press selected chromatographic condition: Elite C18 chromatographic column, moving phase: methyl alcohol: 0.05mol/L acetate-sodium acetate solution (methyl alcohol and acetate-sodium acetate solution volume ratio 55:45), flow velocity: 0.8mL/min.Sample introduction 10 μ L carry out liquid-phase chromatographic analysis, and the concentration that records iminodiacetic acid is 0.5001%.
Embodiment 3: behind the bio-transformation 6h in the conversion fluid iminodiacetic acid sample concentration confirm
Preparation seed culture medium: ammonium acetate 1%, yeast extract 0.5%, K
2HPO
40.5%, MgSO
40.02%, FeSO
40.003%, NaCl 0.1%, with the NaOH of the hydrochloric acid of 2M or 2M with pH regulator to 7.5.
Preparation fermentation medium: ammonium acetate 1%, yeast extract 0.5%, K
2HPO
40.5%, MgSO
40.02%, FeSO
40.003%, NaCl0.1%, with the NaOH of the hydrochloric acid of 2M or 2M with pH regulator to 7.5.
Above-mentioned nutrient culture media is formed and is represented with mass and size number percent, contains this material of 1g in certain material concentration 1% expression 100mL nutrient culture media.
In the 5L seeding tank, pack into the seed culture medium of 3L; Bacillus foecalis alkaligenes (Alcaligenes faecalis) CCTCC No:M 208168 bacterial classification bacterium liquid (this bacterial classification is as the application of novel bacterial separate case) are inserted in the sterilization back; Inoculum concentration 5% (v/v); 30 ℃ of temperature, cultivate 24h under the condition of speed of agitator 200rpm, obtain seed liquor;
The fermentation medium 30L that in the fermentation tank of 50L, packs into, the seed liquor of 1.8L is inserted in real jar of sterilization back, in ventilation than 0.3:1 the ratio of nutrient solution volume (volume of air of passing through in the per minute with); Speed of agitator 150rpm; Tank pressure 0.05Mpa, under the condition that temperature is 30 ℃, the n-Butyronitrile that adds 90g when when cultivating 1h, beginning is as derivant; When cultivating 6h, conversion fluid centrifuging and taking supernatant 0.15mL is adopted the NaHCO of 1.5mL 1mol/L
3Solution, 0.6mL prepare 2,4-dinitrofluorobenzene acetonitrile solution (volumetric concentration 2%) and 1.5mL distilled water behind 70 ℃ of following lucifuges reaction 40min, add 11.25mL 0.2mol/L pH and are 7.5 phosphate buffer again.Filter with syringe filters.Press selected chromatographic condition: Elite C18 chromatographic column, moving phase: methyl alcohol: 0.05mol/L acetate-sodium acetate solution (methyl alcohol and acetate-sodium acetate solution volume ratio 55:45), flow velocity: 1.2mL/min.Sample introduction 10 μ L carry out liquid-phase chromatographic analysis, and the concentration that records iminodiacetic acid is 0.6845%.
Embodiment 4: behind the bio-transformation 3h in the conversion fluid iminodiacetic acid sample concentration confirm.
Preparation seed culture medium: ammonium acetate 1%, yeast extract 0.5%, K
2HPO
40.5%, MgSO
40.02%, FeSO
40.003%, NaCl 0.1%, with the NaOH of the hydrochloric acid of 2M or 2M with pH regulator to 7.5.
Preparation fermentation medium: ammonium acetate 1%, yeast extract 0.5%, K
2HPO
40.5%, MgSO
40.02%, FeSO
40.003%, NaCl 0.1%, with the NaOH of the hydrochloric acid of 2M or 2M with pH regulator to 7.5.
Above-mentioned nutrient culture media is formed and is represented with mass and size number percent, contains this material of 1g in certain material concentration 1% expression 100mL nutrient culture media.
In the 5L seeding tank, pack into the seed culture medium of 3L; Bacillus foecalis alkaligenes (Alcaligenes faecalis) CCTCC No:M 208168 bacterial classification bacterium liquid are inserted in the sterilization back, and inoculum concentration 5% (v/v) is 30 ℃ of temperature; Cultivate 24h under the condition of speed of agitator 200rpm, obtain seed liquor;
The fermentation medium 30L that in the fermentation tank of 50L, packs into, the seed liquor that 1.8L is inserted in real jar of sterilization back compares 0.3:1 in ventilation; Speed of agitator 150rpm; Tank pressure 0.05Mpa, under the condition that temperature is 30 ℃, the n-Butyronitrile that adds 90g when when cultivating 1h, beginning is as derivant; When cultivating 3h, conversion fluid centrifuging and taking supernatant 0.1mL is adopted the NaHCO of 1.0mL 1mol/L
3Solution, 0.4mL prepare 2,4-dinitrofluorobenzene acetonitrile solution (volumetric concentration 3%) and 1.0mL distilled water behind 60 ℃ of following lucifuge reaction-30min, add 7.5mL 0.2mol/L pH and are 7.0 phosphate buffer again.Filter with syringe filters.Press selected chromatographic condition: Elite C18 chromatographic column, moving phase: methyl alcohol: 0.05mol/L acetate-sodium acetate solution (methyl alcohol and acetate-sodium acetate solution volume ratio 55:45), flow velocity: 1.0mL/min.Sample introduction 20 μ L carry out liquid-phase chromatographic analysis, and the concentration that records iminodiacetic acid is 0.3775%.
Claims (1)
1. the liquid phase analysis method of iminodiacetic acid is characterized in that said method is following:
(1) the iminodiacetic acid standard solution of preparation variable concentrations is got the standard solution of 1 parts by volume, adds the NaHCO of 0.1～1mol/L of 10 parts by volume separately
32 of the volumetric concentration 1～10% of solution, 4 parts by volume; The distilled water of 4-dinitrofluorobenzene acetonitrile solution and 10 parts by volume; Behind 40～70 ℃ of following lucifuge reaction 20～40min, the 0.1～0.5mol/L, the pH that add 75 parts by volume again are 6～8 phosphate buffer, and the mixed liquor that obtains carries out liquid-phase chromatographic analysis; With DNB-iminodiacetic acid peak area is that ordinate, iminodiacetic acid (salt) acid concentration are horizontal ordinate, the drawing standard curve;
(2) get solution to be measured 1 parts by volume that contains iminodiacetic acid, add the NaHCO of 0.1～1mol/L of 10 parts by volume
32 of the volumetric concentration 1～10% of solution, 4 parts by volume; The distilled water of 4-dinitrofluorobenzene acetonitrile solution and 10 parts by volume, behind 40～70 ℃ of following lucifuge reaction 20～40min, the 0.1～0.5mol/L, the pH that add 75 parts by volume again are 6～8 phosphate buffer; The mixed liquor that obtains carries out liquid-phase chromatographic analysis; According to the peak area of DNB-iminodiacetic acid to be measured, contrast the typical curve that step (1) obtains, obtain the iminodiacetic acid concentration data of solution to be measured;
Liquid phase chromatogram condition is following in said step (1) and (2): chromatographic column: Elite C18 chromatographic column; Moving phase: methyl alcohol: acetate-sodium acetate solution; Methyl alcohol and acetate-aqueous sodium acetate solution volume ratio is 55: 45, and acetate, sodium acetate amount of substance concentration are 0.05mol/L in acetate-aqueous sodium acetate solution; Flow velocity: 0.5～1.5mL/min; The detection wavelength is 300～400nm; Column temperature: 20～40 ℃.
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| CN102033116B (en) * | 2010-11-22 | 2013-08-28 | 重庆紫光化工股份有限公司 | Method for analyzing mother liquor of N-(phosphonomethyl) iminodiacetic acid (PMIDA) |
| CN102706986B (en) * | 2010-11-22 | 2014-01-22 | 重庆紫光化工股份有限公司 | Method for analyzing iminodiacetic acid component in N-(phosphonomethyl) aminodiacetic acid (PMIDA) mother liquor |
| CN105021740A (en) * | 2015-08-15 | 2015-11-04 | 杭州新博思生物医药有限公司 | High-performance liquid chromatography analytical method for N1,N1-diisopropyl ethylenediamine |
| CN107091891B (en) * | 2017-05-18 | 2019-07-30 | 湘潭大学 | A kind of chromatogram quantitative analysis of the liquid phase method of glycine and iminodiacetic acid in Diethanolamine Dehydrogenation product |
| CN107621507B (en) * | 2017-08-28 | 2020-01-21 | 湘潭大学 | Liquid chromatography analysis method for simultaneously quantifying glycine and iminodiacetic acid in diethanolamine dehydrogenation product |
| CN113088503B (en) * | 2021-04-27 | 2023-01-10 | 浙江工业大学 | O-succinyl mercaptotransferase mutant and application thereof in L-methionine synthesis |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6359119B1 (en) * | 2000-05-24 | 2002-03-19 | Mallinckrodt Inc. | Formulation of Tc and Re carbonyl complexes using stannous ion as the reductant for pertechnetate and perrhenate |
| CN1594281A (en) * | 2004-07-05 | 2005-03-16 | 四川省天然气化工研究院 | Process for preparing iminodiacetic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6359119B1 (en) * | 2000-05-24 | 2002-03-19 | Mallinckrodt Inc. | Formulation of Tc and Re carbonyl complexes using stannous ion as the reductant for pertechnetate and perrhenate |
| CN1594281A (en) * | 2004-07-05 | 2005-03-16 | 四川省天然气化工研究院 | Process for preparing iminodiacetic acid |
Non-Patent Citations (1)
| Title |
|---|
| 韦志明 等.亚氨基二乙酸的高效液相色谱测定.《理化检验-化学分册》.2002,第38卷(第4期),192-193. * |
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